


No Refunds

by Zohar



Category: Catherine (Video Game)
Genre: Catharsis, Gen, Other, Self-Discovery, Transphobia
Language: English
Status: Completed
Published: 2019-02-28
Updated: 2019-02-28
Packaged: 2019-11-06 23:23:05
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,832
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17949140
Author URL: https://archiveofourown.org/users/Zohar/pseuds/Zohar
Summary: An anecdote about Toby's first time. Based on the game's Good Katherine Ending.





	No Refunds

\-----------  
[Present Day]  
\-----------

"Alright, let's start by having you tell me your name." Said the calm voice of a man holding a clipboard and an ink pen. The person to whom he spoke laid relaxed on a therapy chair in front of him, facing away.

"Tobias Nebbins, Toby for short." Toby's eyes wandered around the room while his head stood still and his arms folded on his chest. He took in the unremarkable scenery of the therapist's office he'd finally gathered up the courage to go to. His appointment was with a reputable doctor who specialized in sexuality and mental trauma.

"And why are you here today, Toby?" The man tapped his pen, signaling he was prepared to write and take notes.

Toby took a deep breath before answering the question and closed his eyes. He'd never thought he would need to see a therapist and yet, here he was. There was a small amount of guilt and shame at his predicament in addition to the embarrassment. "Because a friend told me I should talk to a therapist about my issues."

"What sort of issues are you having, Toby?"

"This is strictly confidential, right? I've only ever talked to one other person about this and they were the one who told me to see a therapist."

"Yes, nothing you say here will leave this room."

"Okay.. Well, you see, for the longest time I had these negative feelings that were eating away at me. Feelings of anger, confusion, regret, you name it. And I've been hiding those emotions ever since I lost my virginity a few years ago. To a trans woman." Toby left the air open for a response to see how the doctor would react to that last part.

"..Hm? Please, continue." He said nonchalantly. The only sound in the room came from the movements of his pen.

Toby felt a sense of relief when there was no apparent judgment in his tone. As one of his fears was that he'd find himself confiding in someone who was less than professional. "Do you.. want me to describe it?"

"The details of your sexual experience with her? Yes, if you don't mind. Knowing what happened could help me determine the root of your affliction."

"Affliction? I don't really know if I'd call it that, but.. if it helps you to help me figure this out, so be it. I'll start from the beginning, when the girl I had a crush on finally accepted my advances and took me to her place."

\---------------  
[Three Years Ago]  
\---------------

"Hey, do we really have to turn out all the lights? It's pitch black in here and I want to be able to see you, Erica." Toby whined as he laid on Erica's bed in total darkness. He was on his back, completely naked and waited nervously for her while she prepared herself.

"I know, but I don't want you getting too excited, Toby. You'll be able to see me as much as you want later, okay? For now just let me ease you into it." Erica got on the bed and crawled towards Toby. She kissed her way up his body until she reached his face and gave him light kiss on the lips then pulled back. "Part your legs for me and hold them up with your arms."

"What?? Why??" Toby hesitated at first but when she pushed them open herself he obliged her request. "What are you going to do?" Just as he asked that, he felt something pressing up against his anus. "Whoa! Hey, wait a minute! What in the world is that?"

"My finger." Erica replied curtly.

"That doesn't feel like a finger. Can we turn the lights on now? Please? This is weird."

"No Baby, not yet. Just relax, okay? Leave everything to me." Erica gave one firm push and the mysterious object went inside Toby, causing him to shriek.

"Aygh! You sure about this?! Are we even doing it right? It kind of hurts. I wasn't expecting sex to be like this!"

"Yeah, trust me. This is how it works. The girl gives the guy a prostate massage first and he returns the favor with the resulting boner. You'll get used to it soon and it'll start feeling good, I promise." Erica picked up the pace and started gradually moving faster as Toby loosened up. "Mnh.. So tight.." She moaned in a low, barely audible voice.

"W-What did you say?"

"Haa.. Ha.. Nothing. Little less talking now, k? Let's just enjoy your first time.." The lust in Erica's voice was thick when she all but told him to be quiet while she did her thing. "Shh~, Sh~" Gently shushing Toby whenever he was about to say something else.

\-----------  
[Present Day]  
\-----------

"Now at this point, Doc, I knew something was up. But I was so naive back then that I never suspected it would be something between her legs. Or at least something real anyway. I didn't find that out until later."

"Sorry, I know it was your first time and all, but you didn't know you weren't supposed to be the one getting penetrated?" The professional demeanor the doctor had so far finally gave way to a hint of condescension.

"No.. Go ahead and laugh it up if you want, I won't blame you. I was too pure for my own good back then. I thought she was using one of those sex toys women wear in lesbian porn. Without even wondering why she would have one in the first place."

"I'm not going to laugh at you, I just needed a double take. In all my years of experience I've never heard anything quite like that before. I know some people who might even say you were lucky."

"Lucky how? Because my virginity was over nine-thousand? I'd argue she was the lucky one in that case."

\---------------  
[Three Years Ago]  
\---------------

Erica was pounding away at Toby and he started letting moans slip once the pleasure kicked in. He tried to stifle them out of embarrassment but Erica told him not to hold back.

"Go on, let me hear it. I wanna hear you enjoying this~" She said seductively and grabbed Toby's dick to jerk him off in matching tempo.

"H-How much longer is this going to take? I'm about to lose it." Toby was getting close to cumming and he didn't want it to be this way. Erica let go of his dick and grabbed his feet by the ankles. Toby was able to let his arms relax now that Erica was holding up his legs for him, but her thrusts became more aggressive. After about a dozen more pumps from her, he felt something warm squirting out into him. Toby wrote it off as being his own bodily functions reacting to the stimuli.

"Ahh~ Alright, now its your turn to do me. Let's switch places." Erica said after pulling out. She held onto him so Toby couldn't try to get out of the bed and turn on the lights while she took the position he just had on her back. Reaching for his dick, she grabbed it and massaged her hand around it a bit before aiming his tip at her entrance.

"Why is your hand so wet?" Toby asked, wondering what Erica had just coated his dick with.

"Lube. Come on, hurry up and push it in." She smacked his ass cheek with her other hand and held it there while the one that still had some lube on it was doing things to herself that made sticky noises, which Toby couldn't see.

"Alright, here goes. Goodbye to my v-card!!" Toby gave her one good push and it went in with minimal resistance. Erica was tight, warm and welcoming as she literally sucked him deeper inside of her. "Hoo~ This is incredible!!" He cried out once he found his rhythm.

"Glad you like it. Congratulations on losing your virginity." Erica began squeezing and pushing back against his thrusting. "Was it worth it?"

"Was what worth it?" Toby was too delirious in his passion to know what she meant. At first he thought she might have been referring herself and his pursuit of her to this point, but Erica revealed her dirty mind with her answer.

"You know.. Getting it in the ass first.." Her tone shifted to a more lascivious one and her arousal was clearly at its highest point yet.

"Totally, I already forgot about that."

\-----------  
[Present Day]  
\-----------

"..is what I said but it was still in the back of my mind the whole time. Like her cum that was dripping out of my ass. It was ruining my concentration while I was trying to focus on her." Toby made no effort to hide his annoyance. "In my mind I was going, 'I know that's not what I think it is, I know that's not what I think it is' followed by 'Just ignore it and get this pussy.' Because you know, that's what I thought it was! A pussy! Not an ass! You have any idea how much that messed me up?" To show he was getting agitated by the memory, Toby propped himself on his elbow and turned to face the doctor for the first time since their session started.

"How did it mess you up, Toby?" The doctor responded calmly while making eye contact.

"By turning me on to shemales and crossdressers. I used to be a simple guy who only wanted a woman with a nice pair of heels. Now she's gotta have heels and a dick, otherwise I'll have a hard time getting it up. And I know that's because of how I had my first time."

"Do you blame her?" There was a moment of silence between them while Toby thought it over and the doctor continued to take notes on his clipboard.

"... I can say I used to. That's where the confusion and anger came from. But I'd never let it show, especially around Erica. If not for her I'd probably know a lot less about myself today." Toby turned back around to his original position and resumed his story.

\---------------  
[Three Years Ago]  
\---------------

"You forgot? That's too bad. I was hoping you'd remember it forever." Erica said coyly. They both knew he wouldn't be forgetting anything from his experience with her any time soon.

"Erica..! I'm about to cum!" Toby strained out the words.

"It's okay, do it inside!" Her voice filled with excitement and the sticky noises her lubed hand made sped up twofold.

"Anghh~!" Toby groaned as he let it all out inside her. His whole body shook and he became momentarily paralyzed by the pleasure. "Ha.. Ha.. Wait..! I wasn't wearing a condom!!" He cried out upon realizing what he'd done. Once the orgasm passed over and Toby regained control of his body, he pulled out of her in a panic.

"Don't worry, it's fine. You just lie down and rest for a moment. You were so great you've earned it. I'm going to go clean this up and be right back, k?" Erica hopped off the bed and rushed out of the room without turning the lights on.

\-----------  
[Present Day]  
\-----------

"I swear, the way she ran out of that dark room so effortlessly was the most impressive thing I'd never seen. Girl was like a ninja using the skills she mastered as a waitress. When she came back and finally turned on the lights she was wearing a sexy pair of red hot pants with matching high heels. No doubt a means of distraction to hide her dick from me. And it worked like a charm because I couldn't take my eyes off those heels." Toby let out a reminiscent sigh at the mentioning of heels, thinking back to his simpler days.

"So when 'did' you find out she was trans?" The doctor put emphasis on the word 'did' to imply it was time to get to the point.

"A few days later ... When I was stupidly bragging about it to our friends. I was so proud of losing my virginity and I thought for sure they were going to be jealous of me because I scored with Erica. Nope. These guys went to school with her. And the whole time they knew the woman I was so infatuated with was once a man. If it weren't for my big mouth, I might have avoided getting the bomb dropped on me by somebody else. I know she would have told me herself eventually, but hearing it from one of the guys made it worse. I won't say who broke the news, but at least he tried to be gently about it. I'll never forget the way he said it. 'She'll always be Erica to you. That's what's most important. But to us, she used to be a guy named Eric.' And then he went on to say something about how that's why he never dated her. I was barely paying attention anymore at that point, too in shock, you know? Because it was all coming together."

"Yes, I understand. So did you do or say anything to her about it? You weren't confrontational, were you?"

"No, of course not. Like I said, I kept all that bottled up inside. But she'd soon come to find out I knew. Weirdly enough she acted like it was no big deal and stayed being as friendly as ever. That's why I couldn't turn her away, she was just too nice and I couldn't bear to hurt her. This inevitably caused our relationship to take the friends with benefits route. Despite what was going on in my head."

"What sort of thoughts were you having?"

"'Eric. Eric. Who the hell is Eric?!' That name tore at me because I couldn't perceive how some guy I'd never met trapped me in a relationship with him. There was a part of me going, 'you're sleeping with another man' and it pushed me to avoid her. While another part was saying 'you know that's not true' and pulled me back. I reached an emotional equilibrium by acknowledging her as '90% female, 10% male' and was content with that for a while."

"Why do you say 'for a while,' did something change?"

"Yeah. One of our friends got married. I was at their wedding taking pictures and when I saw him so happy together with his new wife, it hit me hard. I realized just how much I wanted what he had, but I felt like it would never happen for me. That's when Erica draped herself around me and said 'We'll always have each other.' To which I couldn't hold it in anymore. I deadnamed her and said I wanted my v-card back.."

"That can be very hurtful to a trans person. How did she react?"

"She wasn't phased in the slightest and took it in jest. All she said was 'Once that hole is punched there's no refund.' And of course I had no come back to that. It was the sickest burn ever when you realize she literally took both of my virginities in one night."

"She sounds like quite a strong woman. What happened after the wedding? Did you continue seeing each other?"

"Not only that, we started seeing each other more often. As time went on I made peace with my inner turmoil. I became addicted to Erica and the latent transphobia that tore at me was purged through all the intimacy. But I could never feel like it was completely gone. So I started having private conversations with someone whom I felt was qualified to give me consolidation on the matter."

"Who?" The doctor's tone and ceased hand writing movements suggested he was making a territorial gesture.

"The only other trans person I know, my friend Rin. They're the one who told me to come see you, Doc." Toby sat up in his chair and faced the doctor, knowing their session was coming to a close.

"Is that so? ... Why are you really here today, Toby?" The doctor put away his pen and clipboard and gave Toby a discerning look.

"I had to take this one last step to help me put all my ducks in a row. Because if there are any doubts or insecurities still lingering inside my heart, they need to be eradicated."

"Well, I can tell you one thing, you aren't transphobic. So why is that so important to you?"

"I guess that's the point, Doc. I needed someone like you to tell me that. Once I've confirmed the strength of my integrity, I can move forward knowing I'm ready."

"Ready for what?"

"To propose to my girlfriend. If I'm going to ask Erica to marry me, I have to make sure I'm as rock solid as she is first. I decided I want to be happy. And I want to be happy with her. Because once I make that commitment, there are no refunds."


End file.
